


Luck with an F

by thedevilchicken



Category: Black Sails
Genre: Anal Fingering, Anal Sex, Cock Warming, Drunkenness, First Time, Friends With Benefits, Kissing, M/M, Overstimulation, Public Use, Rimming
Language: English
Status: Completed
Published: 2016-04-24
Updated: 2016-04-24
Packaged: 2018-06-04 04:51:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,209
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6642034
Author URL: https://archiveofourown.org/users/thedevilchicken/pseuds/thedevilchicken
Summary: <blockquote class="userstuff">
              <p>There are times Jack thinks he's a very lucky man.</p>
            </blockquote>





	Luck with an F

**Author's Note:**

  * For [lionessvalenti](https://archiveofourown.org/users/lionessvalenti/gifts).



> Set pre-series, while Jack and Anne are on the Ranger's crew and there's as yet no hint of the Urca de Lima or everything going to hell in Nassau!

There are times Jack thinks he's a very lucky man. 

Perhaps piracy was not exactly his lifelong ambition. He'd say it's fair to assume no man dreams himself a pirate as a boy, at least no man who has even the most rudimentary understanding of the rather unsavoury reality dwelling there beneath its shiny brightwork; it's damned hard work for the most part, hauling this and bracing that, caulking, careening, tacking, luffing up. It's not all great guns and musket fire and gold doubloons by the fistful and frankly, great guns and musket fire aren't all they're cracked up to be. Especially when gold doubloons have scarcely ever crossed his palm, let alone filled his fist. 

Perhaps piracy was not his lifelong ambition. He supposes he may have made a fair accountant for all the quartermaster's penny-pinching he performs these days, a fair lawyer since he speaks so well, a physician but for the fact he's not overly fond of the sight of blood when it comes to it. He's seen ships' surgeons up to their elbows in a man's intestines and that sort of stuff just wouldn't come out of his clothes no matter how hard the launderers scrub. And besides which, for his litany of grievances, his compendia of complaints, he loves the life. Yes, he'd prefer untold riches to a berth beneath a flapping black flag, but he's hardly alone in that ambition. That's one of many reasons many men enter the profession, after all. 

So, he puts to sea out of Nassau and calls the Ranger men his brothers, even if they're rather more of them rather more dull-witted than he'd like to think of as a blood relation. They spend their hard-won coin on drink and whores once they've sailed back home, and they put up their tents on the beach under the stars to be free of the roll of the sea just for a while. Anne likes to stare into the night sky when they've strayed away from the lanterns and strolled away down the sandy beach. You don't seen the sky like that in cities, she says. In her more poetical moments, she says the night sky full of stars is what makes her feel free. He doesn't ruin the moment by saying what makes him feel free is the coin in his purse. 

Tonight, he has coin enough to feel his freedom for days, but he has no particular immediate compulsion toward spending it. Tomorrow, he might commission himself a new coat from the tailor in town. He might procure a new knife that will fit snug into his boot-top without damn near slashing his leg to the bone in the process, or a book that he'll read with his boots off on the beach, lounging in the midday sun with his glasses on his nose while Anne rolls her eyes from the shade beneath her hat. Perhaps he'll settle for several bottles of rum to drink the two of them into a stupor, but there'll be something. He thinks he'll never be a rich man as long as he has a rich man's taste.

But tonight there's nothing in the whole wide world for him except Charles Vane. 

\---

Charles likes to pretend he's indifferent. 

He'll sit at his desk in the Ranger's captain's cabin and he'll study the charts and plot a course to intercept their next new prize or he'll just pretend he's doing all of that instead, the instruments laid out but the precise manner in which he shifts them about the chart seems quite arbitrary. Jack should really know that at this point in his career because frankly he's been watching him work for years now, quite frequently and from quite close quarters. 

So, Charles will work or he'll play at working and some nights, some days, some sunny mornings, some stormy afternoons, Jack's there with him. He goes down on his knees on the Ranger's creaky wooden boards and while Charles works, Jack works too. He opens up Charles's worn old leather trousers and while he's careful not to knock his head against the desk, he takes Charles's cock into his mouth. 

The first few times, he was terrible at it. The first few times, he put his hands on Charles's thighs and squeezed and had them swatted away. The first few times, he teased the tip of his tongue at the head of his cock as if perhaps that might speed along the process, but Charles just pulled back and tucked himself away and moved on with his work, and left him frustrated there down on his knees with an erection he knew better than to touch. The first few times, Jack used to think the rules were somewhat difficult to articulate; these days he knows they're simple in almost the extreme: Charles is in charge, and if Jack keeps still and does nothing he's not told to then in the end they'll both be satisfied. 

So now he doesn't suck. He tries hard not to swallow. He's not allowed to touch, either Charles or indeed himself. And Charles puts his cock in Jack's mouth so he can hold it there, or bends him over the desk and puts it up his arse like it's just there for safekeeping, and he works like that or seems to even though it must be awkward. Jack wonders if that's part of the point. 

Of course, sometimes they don't do a single thing for weeks while Jack whispers obscenities in passing as they go about their business, teasing close by Charles's ear though there's always real intent behind it. Jack's found he has a talent for it, murmuring all kinds of filth till Charles looks at him with those sharp, light eyes and it's obvious what's coming next. Jack pushes just one step further, calculating, and then the next thing he knows, Charles is fucking him on the fo'c's'le, bent perilously over the taffrail, up against the mizzenmast at midnight with their trousers round their knees. The whole crew knows it happens because more than likely they've all seen it happen. After all, there's times Charles conducts entire meetings with his balls tucked up inside Jack's mouth, Jack's jaw and knees aching so nearly painfully, and he'll kneel there, his cock almost desperately hard as Charles's rests against his cheek, until he lets him up to flex his jaw and join in the conversation. 

There's times when Charles's cock is in him while they make plans around the captain's table and it's so commonplace by now that it's never mentioned, which frankly just makes Jack enjoy it more, when he's talking and there are eyes on him and Charles's cock is filling him up from behind. Charles uses him in front of them. Even the thought of it sends tingles all the way down to his incipient erection. And he'd stroke himself rather pitifully there in front of them and to the devil with the embarrassment if only he thought Charles would approve. Of course, he wouldn't. There are rules.

Then, afterwards, Charles will pull back and pull out, wrap his hand around his own cock and ask him if he wants it, the answer to the question jarringly straightforward. Sometimes Jack's his usual sarcastic self and says _well of course not, Charles, that's why I'm down here on my knees_ or _oh, I'm feeling quite indifferent to your cock today, Charles; why don't you bugger the bosun's mate?_ And Charles will smirk because he knows him far too well to ever believe he's indifferent, just as Jack knows him in return. And sometimes he'll say yes, just plain, bald _yes_ , and Charles will tease his lips with the tip of his cock or tease his arsehole with the tip of his cock and make him say it again, make him say it _again_ , say _fuck me_ , _Jesus Christ just fuck me_ , _for God's sake, put it in me_ , because he's wanted it for an hour by then, sometimes. 

Charles chuckles, but only till he's in. After that, he's usually far too involved in the sodomy to speak, even if Jack sometimes keeps on jabbering until Charles groans and jerks and finishes inside him, his tanned hands tight at Jack's pale hips. Then Charles might finish him off with his hand while he's still inside him, might tell him to go ahead and touch himself so he'll finish too while he thumbs the crack of his arse and makes him shiver. Nights like that, Jack always comes last. Honestly, he'd say it's worth the wait when it finally happens. 

Of course, those aren't the only ways it happens. Of course, Charles is far from being predictable. Of course, there are nights like tonight. And honestly, nights like tonight, he's remarkably glad they met. 

\---

By the time they met Charles, Jack and Anne had been propping up a bar on the Tortuga seafront for a fraction more than a week. 

They'd made their way there basically because it had seemed rather like a good idea at the time, no real reasoning behind it. Of course, it wasn't exactly the case that Jack's plans always went, well, _to plan_ , and there they were living on their depressingly dwindling and already meagre funds while every captain of every ship that came into the bay turned them down flat. And rather more rudely than was strictly necessary to boot, Jack thought. 

He understood, of course: they were something of a pair of misfits in Tortuga, he and Anne, her a woman in a distinctly masculine profession and him in possession of a vocabulary extending far past profanity of the Anglo-Saxon persuasion and the proper names for all the proper ship-rigged sails. They didn't seem very much like pirates at all, at least not in the most traditional of senses, and so they indulged instead in that most time-honoured of piratical pastimes: drinking. 

"I'm going to find a place to piss," Anne said, ever direct and to the point, and wandered away across the rather crowded room to do so. Jack, for his part, made his way back to the bar and purchased a fresh bottle of rum from the barkeep for the two of them, though values of 'fresh' seemed in its case quite dubious. The bottle was dirty and he couldn't quite say what with, though he found he was drunk enough not to be particularly perturbed by that. 

Of course, that meant he was also drunk enough to trip more or less over his own two leaden feet and go skittering into the solid back of a man at the end of the bar. Said man turned, his shirt soaked through with toppled rum; he eyed Jack for a second as Jack stood there most uncharacteristically dumbly, and then he slapped him straight across the face, left him with a rather unpleasant sting. Jack recalls gawping most unbecomingly and muttering, rather dimwittedly, " _Ow_."

"You spilled my drink," said the fellow covered in the rum. 

"Yes, I did," Jack replied. 

"So why are you staring at me like I'm a whore with her tits out?"

"Well, I rather expected a fist to the jaw at the very least," Jack said.

"So you _meant_ to start a fight?"

"No." Jack frowned. "No, not at all."

"So why are you complaining?"

"You don't think slapping a man's face is just a mite insulting?"

The fellow smiled and raised his brows and cocked his head in just the way that clearly said the insult had been intentional in its entirety. Jack said, " _Oh_ , I see," and he held up the bottle in his hand that somehow, and only the good lord himself knew exactly how that was, hadn't ended up dropped on the floor at some point during Jack's little circus act. "Look, at least let me pour you a drink."

The fellow held up his glass, his hand scuffed and calloused, his fingers all rings and Jack poured as he wondered to himself just how many of those rings had been plucked from dead men's corpses once the smoke of guns had cleared. The rum overflowed the glass while he was staring and he cursed, but the man just laughed and licked his fingers clean while Jack gawped and gawped some more. He turned away. Jack shook his head and took that as his cue to leave; he returned to his table just as Anne sat back down in her seat and pulled her hat down low on her brow. Jack, on the other hand, had rarely been able to bear wearing his hat indoors. It always seemed less couth than made him comfortable, even if he'd had designs on entering trade as a buccaneer, where _couth_ seemed a little superfluous.

Jack talked the rest of the the night, the way he always did and always had and always has, and Anne sat by in her usual fashion, perhaps listening and perhaps not at all. She's never seemed to feel obliged to answer when he speaks and he's never felt particularly affronted when she doesn't; after all, they both know he's often speaking just to ward off silence. Or, to be less charitable about the situation: he's speaking just to hear the sound of his own voice. He does rather like it.

He talked the rest of the night while Anne spun a coin from her purse on the scarred old tavern tabletop and he eyed the man at the bar who was wearing his drink as a stain on his shirt. Every now and then, he looked back. Every now and then, he caught Jack's eye with just a fraction of a smile and his gaze raked Jack's body head to toe before he turned back to his companions. Jack had to admit he found the way he looked at him quite thrilling, once he'd finally ascertained that it was indeed him that he was looking at and not some tit-flashing floozy sat somewhere behind; the man at the bar seemed amused when he checked. And then, after an hour or more or close to two or practically fucking him raw with his eyes across the room, the man put his glass down on the bar for the very last time and he left. Jack watched him go. Then he turned back by the door, raised his brows at Jack and _then_ he left, and _then_ Jack watched him go.

"Go up to bed without me," Jack told Anne, leaning over by her ear. She threw back what was left in her glass but poured another in a way that said she might go on to bed without him but she'd damn well finish the bottle first. Jack, on the other hand, pushed himself rather unsteadily to his feet and left through the front door. And then, he found himself tugged rather unceremoniously into the adjoining alleyway. 

"You've been watching me," said the man from the bar, rather closer then than was anticipated. 

"Yes, I have."

"You looking for a friend or a fuck?"

Jack shrugged. "Why not both?" he said. 

The man chuckled as he walked him up against the tavern wall and Jack has to admit he went quite willingly. "Let's start with one then we'll see about the other," he said. 

Jack also has to admit he wasn't quite expecting quite what happened after that. His rum-addled brain admittedly hadn't thought it through to any great extent at all but going down on his knees in the rather dirty alleyway had seemed quite distinct as a possibility, particularly as there was a lady of the night working similar magic a few yards away from them, on her knees past empty boxes with a loud, enthusiastic seaman. Perhaps the fellow even felt like doing the same himself, going down on his knees and sucking Jack's cock till he made sounds most unbecoming a pirate, and heaven knew Jack wouldn't exactly have protested. 

But what he did was shove Jack up face-first against the wall, fumble at Jack's belt and tug his trousers down around his knees. He slapped Jack's arse and made him yelp then he was down on his knees in the dirt behind him, palms parting Jack's cheeks, and Jack's eyes went wide as fucking saucers in surprise as the fellow's tongue met with his arsehole. He moaned. He groaned. He parted his thighs just as wide as he could and felt that tongue lick and flick and tease and lap and Jesus Christ, he'd never felt anything quite like it, almost laughed he was so drunk and so aroused, his cock hard as a fucking deck plank and throbbing like he'd caught it in a door, but that would have been particularly rude, he thought. Jack's been known to be rude, but being rude in the midst of a sex act just seems vulgar. 

Then the man stood back up while Jack ached. He heard the rustle of clothing, heard him spit, knew precisely what he should expect and when the head of his cock met Jack's arsehole, when he pushed close, pushed tight, pushed up inside, all Jack could do was half-stifle a groan against the crook of his arm. He hadn't imagined being fucked in the arse in an alley by a perfect stranger when the night had begun, but in that particular moment there was very little in the world he wanted more than that full cock in his arse and those hard hands at his hips and that hot mouth at his neck. The man moved, shoved up tight against him, did it again, bucked his hips, thrust hard, and Jack frankly could not have cared less that his face scraped up against the wall and his palms were grazed because he hadn't had a decent cock in years. Anne knew what he liked but it wasn't exactly the same when she oiled up the nearest solid object of even vaguely appropriate proportions and buggered him with it. He did, however, appreciate her willingness to assist.

A hand went around his cock and Jack recalls spilling his stuff up against the wall while the cock in his arse jerked and pulsed and then, finally, pulled out. The man patted Jack's arse. Jack, rather weak-kneed, still drunk, feeling remarkably well-fucked for a chance encounter in an alley, turned around and leaned himself against the wall. 

"Charles Vane," said the man, and held out his hand. Jack shook it, despite the fact he was still standing there with his cock on display for all who cared to see. Fortunately, the only one there who cared to see was Charles Vane.

"Jack Rackham." 

"I know who you are, Jack," said Charles Vane, looking highly amused. "You've been harassing captains up and down the beach for a fucking week. You don't look like much of a pirate." 

"I know it's hard to believe but I've heard that before," Jack said.

"You don't say."

"But I most certainly _do_ say."

Charles looked at him precisely like he wasn't sure at all what to make of him, like he wasn't sure if he was joking or somehow completely serious. But what he said in the end was, "I'm on the Ranger. Come tomorrow." He seemed to ponder for a second after that, while Jack tucked himself back in. "And bring the woman. I saw her come this close to gutting a man with a fork when he pinched her arse so I'd expect she's a good hand in a fight." 

He didn't wait for an answer. He flashed a quick little smirk of a smile and then he turned and strode away. 

It seemed Jack had had something of a change of fortune. 

\---

He likes to have sex with Anne. She's pretty and she's fucking deadly and he loves her quite sincerely. He can - and does - spent entire evenings in the worship of her body, stripping her down to her pale skin that never seems to tan perhaps because she never seems to show it, and it's not simply because he thinks she deserves it but because, quite simply, he adores her. They're companions in all things and know each other just as well as two people ever can. She'll always have him if she wants him, no choice to make, no hesitation in it. But then there's Charles, and Charles is something else completely. 

Jack's always been quite broad of horizons where matters of sex were concerned and Charles, it turned out, has a broadly similar approach. Jack rowed out to the Ranger the day after they met and found Charles Vane was its captain. Charles ushered him into his cabin and closed the door behind him, then proceeded to bite Jack's neck and lick Jack's lips and grope Jack's arse like he was making an attempt to chomp him into pieces and then eat him like a shark. 

It was unexpected but exhilarating, getting his hands on Charles's skin under his rum-stained shirt, his hands into his hair, around his cock; they kissed shoved up against the cabin door, pushing against each other till Jack came without even unbuckling his belt, let alone pulling down his trousers, and Charles took off his shirt and cleaned himself up then strode to the stern and tossed said shirt straight out of the window. Jack remembers laughing. He remembers the mischievous way Charles smiled. Then they brought in Anne from the deck outside and Charles asked them both to join his crew. They did. He likes to think the rest's history.

Sometimes, Charles goes down on his knees and sucks him. Sometimes, Charles climbs on top of him and rides his cock like a champion because hell if he cares what anyone thinks of him, least of all Jack, or most of all Jack. And they're not really lovers, per se, because Charles has the Guthrie woman whenever she comes calling and Jack has Anne when and where and how she wants him, but Jack can live with that, that uncertainty, that odd sexual camaraderie. Especially nights like tonight. 

They're drunk, of course, because they spend a good portion of their time that way. But tonight Jack's in Charles's tent on the beach at Nassau rather than his own with Anne, stripped completely naked just like Charles is. They drink more, spill it on each other's skin oh-so-very-accidentally, Charles licking rum from Jack's chest while his oiled-up fingers press lazily inside his arse. Jack's already come twice tonight in quite quick succession; Charles has already teased the tip of his cock with the tip of his tongue, backed away then started again, backed away then started _again_ , teased him for an hour or more, snickering with it till Jack was half-crazed and fucking writhing, then he let him come in his mouth till frankly he thought he might pass out and sleep for a week. Of course, Charles just washed his mouth out with rum then he started again, teased him again till he was hard enough that he could climb astride his hips, finger his own arse with oil then ride him till he came all over Jack's chest. Charles is unapologetic. Jack likes that about him.

It's nights like tonight that Jack feels oddly lucky. He stretches out on his back in Charles's makeshift bed and he pushes his hips down against Charles's weather-worn fingers, and he feels something like the luckiest man alive, so says the drink. Charles pulls back and then in the flickering lamplight he moves up over him, looks down at him, smiles a lazy, rum-soaked smile then sits back on his heels and oils his cock while Jack watches. Charles Vane is a hell of a pirate and a hell of a man, strong-willed and almost the living image of some kind of goddamned Grecian statue when he's naked, if Jack finds the desire to wax poetic on the matter. And when he shifts forward, puts his cock to Jack's arse and then pushes inside him, Jack's hard again despite himself. Every thrust of Charles's hips, every inch of his cock moving in him, every touch of his hand to his damned touchy erection makes him tense and shiver and twitch and jerk like he's lost all control of his limbs because apparently on nights like this, that's precisely what it pleases Charles to do to him. On nights like this, Charles doesn't pretend indifference. Charles doesn't pretend he doesn't want him. He does, and badly. 

He'll stay the night in Charles's bed with him like he's done so many times before and in the morning, he might go out into town and buy a new coat from the tailor. He might buy a knife or a book or several bottles of rum, then he'll see to all the ship's stores being replenished and in a few days' time they'll be back out to sea. They're pirates, after all. The sea's where they belong.

And so, perhaps piracy was not exactly his lifelong ambition, but sometimes Jack would still say he's a lucky man despite it. 

Tonight is one of those nights.


End file.
